Use of compounds with a nitrogen-oxygen heterocycle

Details Use of compounds with a nitrogen-oxygen heterocycle Use of compounds with a nitrogen-oxygen heterocycle

2001-11-02

2003-10-28

Padmanabhan, Sreeni (Department: 1617)

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Having -c-, wherein x is chalcogen, bonded directly to...

C514S228800, C514S114000

Reexamination Certificate

active

06638957

ABSTRACT:

This invention relates to the use of compounds comprising a nitrogen-oxygen heterocycle as an active ingredient and the salts, esters and salts of the esters thereof and for the therapeutic and prophylactic treatment of infections in humans and animals, caused by viruses, bacteria, fungi and parasites, as well as the corresponding treatment and the thereof as a herbicide.
In U.S. Pat. No. 4,209,512 phosphono acid derivatives comprising a nitrogen-oxygen heterocycle are disclosed as insecticides and acaricides.
It has now been found, surprisingly, that compounds according to claim 1 comprising a nitrogen-oxygen heterocycle may be used as an active ingredient for treatment of the above stated infections and as a herbicides. It has been shown by experiments, that the effect of the compounds is based on an inhibition of the 1-deoxy-D-xylulose-5-phosphate-(DOXP) metabolic pathway, which can be proved in micro-organisms and plants, but not for human beings. Accordingly, the compounds according to the present invention show an anti-infectious effect against viruses, bacteria, fungi, uni- and multicellular parasites and as herbicides. Further developments of the invention are defined by the subclaims.
Compounds used according to the present invention correspond to the general formula (I):
in which Y is a C
1-3
alkenylene group, substituted with the substituents R
1
and R
2
and optionally with the substituents R
3
to R6,
in which R
1
to R
8
are the same or different and are selected from the group, which consists of hydrogen, hydroxy, halogen, substituted and unsubstituted alkyl groups, substituted and unsubstituted cycloalkyl (C
0-26
)-alkyl groups, substituted and unsubstituted cycloalkoxy (C
0-26
) alkyl groups, substituted and unsubstituted alkoxy (C
0-26
)-alkyl groups, substituted and unsubstituted amino groups and substituted, unsubstituted thio (C
0-26
)-alkyl groups, substituted and unsubstituted sulfonyl-(C
0-26
)-alkyl groups, substituted and unsubstituted sulfinyl-(C
0-26
)-alkyl groups and substituted or unsubstituierten acyl radicals, in which each alkyl radical, each alkoxy radical and each acyl radical branched or unbranched and each alkyl radical, each alkoxy radical and each cycloalkyl group may be saturated or unsaturated having one or more double or triple bonds and one or two carbon atoms of the cycloalkyl groups may be replaced by nitrogen, oxygen or sulphur atoms and
R
13
and R
14
are defined like R
1
to R
8
or together form an oxo group,
wherein X is the organo phosphorous group
in which R
9
and R
10
are the same or different and are selected from the group, which consists of hydrogen, substituted and unsubstituted (C
1-26
)-alkyl groups, substituted and unsubstituted hydroxy-(C
1-26
)-alkyl groups, substituted and unsubstituted cycloalkyl-(C
0-26
)-alkyl groups, substituted and unsubstituted acyl, halogen, OX
9
or OX
10
, in which each alkyl radical, each alkoxy radical and each acyl radical branched or linear and each alkyl radical, each alkoxy radical and each cycloalkyl group saturated or may be unsaturated having one or more double or triple bonds and one or two carbon atoms of cycloalkyl groups may be replaced by nitrogen, oxygen or sulphur atoms, wherein X
9
or X
10
may be the same or different and are selected from the group, which consists of hydrogen, substituted and unsubstituted (C
1-26
)-alkyl groups, substituted and unsubstituted hydroxy-(C
1-26
)-alkyl groups, substituted and unsubstituted cycloalkyl-(C
0-26
)-alkyl groups, substituted and unsubstituted acyl, silyl, a cation of an organic and inorganic base, in particular of a metal of main group I, II or III of the periodic system, ammonium, substituted ammonium and ammonium compounds which are derived from ethylenediamine or amino acids, wherein each alkyl radical, each alkoxy radical and each acyl radical branched or unbranched and each alkyl radical, each alkoxy radical and each cycloalkyl group may be saturated or unsaturated having one or more double or triple bonds and one or two carbon atoms of the cycloalkyl groups may be replaced by nitrogen, oxygen or sulphur atoms,
or wherein X represents amino group
wherein R
11
and R
12
are the same or different and are selected from the group, which consists of hydrogen, substituted and unsubstituted alkyl groups, substituted and unsubstituted cyclo-alkyl-(C
0-26
)-alkyl groups, substituted and unsubstituted cycloalkoxy-(C
0-26
)-alkyl groups, substituted and unsubstituted alkoxy (C
0-26
)-alkyl groups and substituted or unsubstituted acyl radicals, wherein each alkyl radical, each alkoxy radical and each acyl radical branched or unbranched and each alkyl radical, each alkoxy radical and each cycloalkyl group may be saturated or unsaturated having one or more double or triple bonds and one or two carbon atoms of the cycloalkyl groups may be substituted by nitrogen, oxygen or sulphur atoms,
wherein B is selected from the group, which consists of substituted and unsubstituted C
1-26
-alkenylene groups, in which one C-atom may be replaced by an oxygen atom and one C atom my be replaced by a sulphur atom or two C-atoms may be replaced by a S-heterocycle and wherein each alkenylene radical may be branched or unbranched and may be saturated or unsaturated having one or more double or triple bonds and may be saturated with one or more hydroxy groups, halogen groups or oxo groups.
Preferably R
13
and R
14
together form an oxo group in &agr;-Position to the nitrogen atom.
Y preferably represents a methylene group, which is particularly preferably substituted with two methyl groups.
Compounds, in which B represents ether group (II)
—A
1
—A
2
—  (II)
are advantageous, wherein Al is absent or is a (C
1-9
)-alkylene radical,
and A
2
is absent or selected from the group, which consists of (C
1-9
)-alkylene radicals, a sulphur atom and a (C
3-8
)-heterocycle, which comprises at least one sulphur atom. It is especially preferred that A
1
and A
2
each represent a methylene group.
Also compounds, in which B represents a keto group (III)
are advantageous, wherein A
3
and A
4
, out of which one or both may be absent, are the same or different, may be selected from the group, which consists of (C
1-9
)-alkylene radicals, wherein all the (C
1-9
)-alkylene radicals may be branched or unbranched, may have one ore more double bonds or may be substituted with a hydroxyl group or a halogen group. It is particularly preferred that A
3
is absent and A
4
represents a methylene or an ethylene group.
Preferably B furthermore is a 2-hydroxypropylene group.
R
9
and R
10
preferably represent OX
9
and OX
10
, wherein X
9
and X
10
are the same or different and are selected from the group, which consists of a metal of the first, second or third main group of the periodic system, in particular sodium and potassium, and methyl, ethyl.
Examples for individual compounds are listed in the following:
The following compounds are in particular preferred:
Special features of the above definitions and suitable examples thereof are stated below:
“Acyl” is a substituent which originates from an acid, such as from an organic carboxylic acid, carbonic acid, carbamic acid or the thioacid or imidic acid corresponding to the individual above-stated acids, or from an organic sulfonic acid, wherein these acids may in each case comprise aliphatic, aromatic and/or heterocyclic groups in the molecule, as well as carbamoyl or carbamimidoyl.
Suitable examples of these acyl groups are stated below.
Aliphatic acyl groups are deemed to comprise acyl radicals originating from an aliphatic acid, such groups including the following:
alkanoyl (for example formyl, acetyl, propionyl, butyryl, isobutyryl, valeryl, isovaleryl, pivaloyl etc.);
alkenoyl (for example acryloyl, methacryloyl, crotonoyl etc.); alkylthioalkanoyl (for example methylthioacetyl, ethylthioacetyl etc.); alkanesulfonyl (for example mesyl, ethanesulfonyl, propanesulfonyl etc.); alkoxycarbonyl (for example methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, isopropoxycarbonyl, butoxycarbonyl, isobutoxycarbon

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